Assuming my chain is showing that it's worn and getting close to needing replacement due to chain 'stretch'. I know you can flip single speed chainrings to extend their life when they become worn. Can I flip the chain around to extend it's useful life? I doubt it would double it due to some overlap in wear on rollers, but possibly extend it a bit by putting load on the opposite side of the pins.

I would be measuring different sides of the pins/rollers to see if the wear varied by side. It would not be measuring the same 2 points.
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BenzoFeb 26 '13 at 15:04

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No. As others have said, the main "wear" that a chain experiences is in the plate joints, resulting in "chain stretch" that will be identical either direction. And when you use, eg, a chain stretch gauge you're inherently measuring both sides.
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Daniel R HicksFeb 26 '13 at 16:02

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(Keep in mind that when the chain is in use the front sprocket is bearing on the opposite side of the pins than the rear sprocket. The wear is about as symmetrical as can possibly be imagined.)
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Daniel R HicksFeb 26 '13 at 16:04

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Flipping the chainring on a single speed makes sense as you use the other side of the teeth on the chainring which have not been used before. But with the chain it's a different story: The stretch is independent of directions so reversing its direction won't change anything. Also on the small "rolls" in the chain links on which the chain lies on the chainring I wouldn't expect any effect as they aren't fixed in the links but can rotate and therefore should wear out equally all around their circumference.

The rollers would likely wear relatively evenly, but I wonder about the pins and plates that the rollers rub against under load.
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BenzoFeb 26 '13 at 15:07

@Benzo: A majority of the load (therefore wear) is on the first couple of links going onto the cog - when the chain is virtually straight. Therefore flipping it would not make any difference.
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mattnzFeb 26 '13 at 21:27